Philadelphia Eagles

Title Drought since: 1960

The whole Philadelphia sports scene has seen the championships dry up in recent years, with no team from the city winning a title since this '83 Sixers. But no team has gone longer without gold than the Eagles.

Colin Montgomerie

Title Drought since: Still waiting for a major

Since turning pro in 1987, Montgomerie has been a steady winner, capturing 40 tournaments along the way, but he currently holds the unwanted, unofficial title of "Best Player Never to Win a Major." Monty has finished second in the U.S. Open, British Open and PGA Championship, but has never seen his name at the top of the leaderboard. However, he has won two majors on the senior Champions Tour after being inducted into the World Golf Hall of Fame in 2013.

Toronto Maple Leafs

Chicago Cubs

Title Drought since: 1908

The Billy Goat curse. Leon Durham. Steve Bartman. Whatever it is, generations of Cubs fans have come and gone while waiting to win another World Series for the last century. The Cubs have not even appeared in the Fall Classic since 1945.

Cleveland Indians

Title Drought since: 1948

For years, the Indians were the laughingstock of MLB, not finishing higher than fourth place in their division from 1969-1993. While Cleveland has been markedly improved in the last 15 years, the title drought has reached 60 years and counting.